


Two Heads are Better Than One

by CS_impala67



Series: My Kinktober 2020 fics [23]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Dean Winchester, Dildos, Double Penetration, Double Penetration in One Hole, Kinktober, Kinktober 2020, M/M, Sex Toys, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-10-23
Updated: 2020-10-23
Packaged: 2021-03-09 03:27:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,005
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27167257
Author URL: https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67
Summary: The first finger was a welcome stretch, and Dean sighed as it pushed its way in beside the toy already stretching his ass. He had been begging Cas to try this for weeks, wanting to feel two cocks inside of him at the same time, but he had been fantasizing about it even longer.It had taken a lot of persuasion, but Cas had finally caved and agreed to try it. His only stipulation was that they used a toy for it, and not another person. Which was fine with Dean, as neither of them were into sharing.
Relationships: Castiel/Dean Winchester
Series: My Kinktober 2020 fics [23]
Series URL: https://archiveofourown.org/series/1961551
Comments: 5
Kudos: 113





	Two Heads are Better Than One

**Author's Note:**

> For Kinktober Day 23 I chose Double Penetration in One Hole

The first finger was a welcome stretch, and Dean sighed as it pushed its way in beside the toy already stretching his ass. He had been begging Cas to try this for weeks, wanting to feel two cocks inside of him at the same time, but he had been fantasizing about it even longer.

It had taken a lot of persuasion, but Cas had finally caved and agreed to try it. His only stipulation was that they used a toy for it, and not another person. Which was _fine_ with Dean, as neither of them were into sharing. Dean would never admit it out loud, but he loved how possessive Cas could get sometimes. It made him feel loved, and desired, and all that other sappy crap that he always pretended to hate, but secretly loved. Cas always managed to make him feel all sorts of things he had never felt before, in any of his previous relationships. He had never trusted someone like he trusted Cas; with his heart and his body.

No way in _hell,_ would he has trusted anyone else to let himself be as vulnerable as he was now; bent over a wedge pillow, naked, with his ass in the air, getting stretch to take two cocks.

A second finger joined the first, making Dean grunt at the pressure in his ass. He felt so full already, but he still needed to take a couple more fingers before he'd be open enough for Cas’ cock to fit alongside the dildo.

“Fuck…” He breathed out, sweat beading on his forehead.

“Are you okay love?” Cas asked concerned, as he rubbed a soothing hand up the back of Dean’s thigh.

“Yeah… fuck, it's… it's good, just feel so full.” He managed, pleasure making words hard at the moment. “Keep going.”

Cas work both fingers in alongside the toy, gently working Dean's ass open before adding a third.

“Ngh…fuck!” Dean shook from the intensity, as he tried to relax his muscles to accept the increasing stretch.

“You're taking my finger so well, love”. Cas praised. “Your ass is so hot, all stretched out like this.” He said, as he began to thrust his three digits gently inside.

After finally working in a fourth finger along with the other three, Cas finally deemed the other man ready. He pulled his fingers free, and Dean whined at the loss, before he felt the blunt pressure of his boyfriend's cock at his hole. He held his breath as Cas pushed forward, the pressure so intense, before he managed to breach the ring of muscle.

“Fuck!” Dean screamed, as his ass was stretch to its limit, fuller than he had ever been before. “Wait!” He called out, panting.

“Should I pull out Dean? Is it too much?” Cas worried, concern heavy in his voice.

“No… n-no don't. D-don’t p-pull out. I..I just, fuck...” Dean choked out between gulping in large breaths of air. “I j-just need a minute.” Cas rubbed soothing circles on Deans lower back where sweat had begun to pool. He was so overwhelmed at the feeling in his ass, the stretch so intense, he was having trouble thinking straight. The burn was a delicious mix of pleasure and pain, bordering on too much, but he was determined to take it all. He took deep breaths trying to calm himself; He felt like a live wire, like a lit fuse ready to explode. Every nerve in his body was on edge.

Finally, after was felt like an hour but was probably only mere minutes, he felt his muscles begin to relax, enough that he told Cas he was ready. “Slow... just, just g-go slow.” he warned.

Cas pushed forward again, _slowly_ , and Dean's breathing picked up as see was filled.

“Fuck.” he cursed again, the burn bordering on too much as Cas’ cock pushed, in making room for itself alongside the toy. He closed his eyes and breathed through the agonizing stretch, as his boyfriend finally bottomed out, making them both grunt at the feeling.

“So… so tight, _Dean_ ” Cas growled through gritted teeth as he held still, letting Dean adjust to the impossible fullness in his ass.

“Holy _fuck_! Cas, s-so full!” He cried out.

“Fuck, you did it Dean. You took both cocks. I-I need… fuck! I need to move, Dean, _please_ tell me I can move!” Cas pleaded; voice tight with restraint.

“Fuck yeah, Cas. Fuck me.” Dean begged breathlessly. He felt Cas reach down and grab the fake cock before pulling it and his own back, and thrust them both in.

“FUCK!” Dean screamed as both cocks fucked into him, nailing his prostate. Over and over, Cas thrust in and out of his ass, both cocks fucking him together; the feeling unlike anything he’d ever experienced before.

“fuck, fuck, fuck, Cas…” He babbled as his cock leaked on the pillow beneath him; The assault on his ass bringing him over the edge. He felt his balls tighten before they exploded beneath him, making come untouched. He screamed himself hoarse as ropes of cum shot out of his cock.

“Fuck!” He heard Cas follow behind him, painting Dean's insides with his own release.

They both took a minute to catch their breaths, shaking through their orgasms before he felt Cas pull the toy and his own softening cock out of the abused hole. Dean whimpered at the emptiness. He reached behind himself, to touch his hole and felt it gaping.

“Holy fuck. I'm still wide open.” He stuttered in amazement.

“Yes. Yes, you are.” Cas agreed as he ran the tips of his fingers around Dean's rim. “How do you feel?”

“Fuck, that was amazing Cas. But I'm definitely not going to be able to sit comfortably for a week.” He giggled, still high on endorphins. Cas chuckled with him as they both cleaned up and collapsed on bed together, completely exhausted and spent. Dean fell asleep quickly, thanking his lucky stars that he had this amazing man in his life.


End file.
